Who is Gloria?

Jane continued to watch TV, so I joined James in the kitchen and started talking with him. I hope I can get the date mood right early on. "So what do you do at home, James?"

"Frankly, it's been ages since my schedule was this empty. I'm glad we get to spend some time together, though I obviously have nothing ready."

"Don't worry, I... kinda invited myself anyway."

"Can I ask... What had you hoped would happen this evening? I don't mind you being here of course, I'm just curious what you expected to happen."

"Nothing much, honestly. You're fun at work and I just hoped we could continue that." I paused for a little bit. God, I was so planless. I had hoped this could be a nice date, but I just can't make a great conversation with him. I feel like we need something to talk about. Jane watched the news, but I don't think I want to watch that right now. It's typically just one downer after another. And James doesn't seem like the kind of guy to have problematic opinions that I need to know about first. But he had... "Is that a Switch?"

"Yeah, haven't played it in a while. Life's been too busy recently. Wanna play something after dinner?"

"Sure, let's go for some Mario Kart."

"Oh, it's been ages since I last played some. I hope I'm not that rusty."

"Haha, don't worry. It's been ages since I played Mario Kart too. My brother is a streamer, so I played it with him some years ago."

"Oh, that's cool. Being a streamer sounds like a fun job."

"It can be. If you have a big audience you earn a lot too. But if your tastes change or the kinds of games you don't like stop getting releases, it can hurt your career... Some friends of my brother have that problem."

"Honestly, I wonder if I could do it. With journalism, I made something I liked to do anyway into an actual job. I feel like I could do better than most when it comes to making your hobby your job."

"Well, take it from my brother, you also have to be entertaining. And if you grow big enough you need some moderators. That's how I started out, actually."

"Oh, so you got your job training in the field, huh?"

"Haha, you could say that. Did you not?"

"I mean, I had plenty of internships. But for journalists, they're few and far in-between... I've written about sport and garden utensils and other stuff that I couldn't care less about. Local news that never concerned me. It's... a mess. My CV is a mess."

Eventually, James finished making dinner and we three sat at the table quietly, enjoying his meal. He made some spaghetti with meatballs and tomato sauce. It's a simple dish, but it's weirdly fitting for what is meant to be a gaming evening. I had hoped that this could be a great date but I'll be happy even if we just end up playing games together. I'm not sure how he sees me. I think I want to go all the way with him. I never bothered much with relationships, but I have to end up in one eventually, right? I doubt I'll make a good cat lady. But will I get anywhere if I just go ahead with everything he asks of me? Maybe I need to take some action...

Finally, we played a test round of Mario Kart. In the race, I came in second and James in third. My pride as a gamer is hurt: "Well, we are actually a bit rusty, it seems. Getting beaten by the bots..."

"Yeah, it's a real shame. But at least we can try to improve without either of us having to beat the other one."

"Oh, you're not one for competition?"

"Haha, no, we can be competitive. I just expect us to come first and second next time, so we should still have improved somewhat."

"Hm, I want to raise the stakes a bit..." This is my chance to make a move on him. I have to play my cards right, so that I can steer this in the right direction.

"What do you plan?"

"I don't know yet. The only punishments for these kinds of games are sexual or involve ****."

"Well, **** will be an issue since I don't really drink." Hehe, he fell for the trap. Or maybe he was looking forward to it too. Either way works for me.

"I... want to drink less too. Just one option, I guess."

"I mean if you don't want to, we don't have to. I like the idea, but whatever you're comfortable with." Heehee... I feel like an evil villain who's schemes all came to fruition.

"No no, that's still good. I'm not going to do jumping jacks at 8 in the evening, James."

"Hah, fair enough."

"So I'm thinking we'll do the typical stripping game?"

"Hm, should we play until the bitter end or make a limit? Every cup has four races..." He was thinking. "I have an idea... Maybe we dress back up after every cup. That way, if we want to see each other... we have to win every race. If we want to see each other naked, we have to earn it. Might make it more competitive..." Hell yes, he's got some good ideas of his own. This should motivate the two of us. Well, hopefully. I hope he sees me that way.

"You're on."

"Okay, so my four pieces of clothing are these... A sweatshirt, a shirt, my pants, my underwear. What about you?"

"I'll match you. Shirt, pants, bra, underwear."

"Are you sure? I could see your breasts early that way. Not that I'm complaining, of course, but it might make it too easy for me to get what I want..."

"You say that as if you wouldn't be distracted during the last race."

"Good point, with such a pretty woman beside me, topless no less, that might prove challenging. Okay, you're on. Now I'm motivated." He does see me this way. Mwahahaha, everything went to plan. Soon I might have a boyfriend and everything will be great.

With that, we started the first set of races. Neither of us won the first two races, but then James won the third and I the fourth. We undressed accordingly. He looked more casual, while I gave him something to look at. My breasts might be nothing special, least of all with Donna at work, but breasts are breasts. And if he just goes by size, I don't want anything to do with him either. "Maybe we should have done the other approach..."

"You say that, but... I'm happy with what I earned. Motivates me to do more..."

"Haha alright, we can give it another go." Can't hurt to give his idea another go, I suppose. Even a 2:2 could yield wonderful results! Gloria +5SP (-2SP)

The next cup, we clearly improved. I won the first two races making James topless, while he beat me in the third round. In the last round, a stupid bot overtook us both at the last minute. I looked at his upper body and said "You know, I think I understand you now, maybe we should stick with this system..." I definitely felt warmer, I hope I wasn't blushing that obviously.

"Next time I'll get your pants, off, just you wait."

"Well looks like we both share a goal, huh? But only one can get it..."

The third cup was on. James won the first race, while I won the second and third. James however, managed to eek out a win against me in the last race. Hesitatingly, I pulled down my pants. It was a little bit embarrassing to stand in front of him like that. I want him to see me, but doing it... I could die of embarrassment. Why is trying to date so difficult...

"I'm glad I won. You really are a pretty woman, Gloria. I like your idea for this session..."

Next up was the fourth cup. James beat me in the first race, but I always trained on the harder tracks against my brother. I know Bowser's Castle and Rainbow Road like my backyard, so with a bit of luck I won the other three races. "James, stand up please, I want to see your body in full."

"Only if you do the same in return once I win some more..."

"Fine... The longer you stare at my body, the longer you will be distracted in the cups thereafter." Him watching my body... I have mixed eelings. One the one hand, I want him to appreciate my body, but thinking about a guy staring at my semi-nude body... Well, if it's him. Gloria +3SP (+1SP) "I do have to say, you are a very handsome man. And also sexy. Not everyone needs a sixpack to look good, that's my ideology." He really is a looker. I could have tried to shoot my shot with way worse guys, I'd imagine.

"Well then I'm glad I saved all that effort to get better at Mario Kart. I wanna see what you're hiding under that purple bra..."

"Only one way to get there... if you're up to it."

Ah, the retro tracks. I was never great at them. James beat me in the first two races, and then came the moment. He used a mushroom and a red shell well and got into first, leaving me to eat his dust in 4th. I kind of felt weird about undressing. I had agreed to it, but now doing it, I felt a little bit less inclined to follow up on my promise. I think that's in large part because he had been right. It feels a bit weird standing with exposed breasts around him while all I saw was his underwear. But whatever. Maybe I'll win next time.

"I like your breasts. Can't wait for us to do more than strip."

Let's be real, I know what he wanted to do. And I kind of wanted it too... "You can touch them for a bit." Gloria +2SP (+3SP)

"If you ever beat me four times, you can do the same. I'm not that mean." His breasts? No, he meant his dick, of course. Sly dog... It was some good motivation though, he may have dug his own grave... I am this weird mix of horny and hesitant, it's not great for me. But I think the horny side slowly grew in influence.

In the next cup, I decisively beat him every race. Interestingly, he never tried to lose deliberately, I often had to fight for first place. But a mix of motivation, better items and improving skill made me achieve my goal. James was in front of me, naked. His penis was quite large... "And that this is supposed to fit...?"

"It always does, Gloria. The human body is very adaptable."

"Hmmm... Did you have lots of sex so far?"

"Well, with a couple women, yeah. It's never really been an issue. If we get this far, I'm fine to go slow with you, no worries."

"Oh ho ho, what a gentleman, promising me to go slow with his monster..."

"What about you, Gloria? Have you ever?"

"Yeah, a couple of times. It never lasted. I'm not that interesting of a person and well, unlike someone like Donna or Helen, I don't have the body to make that an issue one can overlook..." Gloria +5SP (+8SP)

"I would disagree on both sides, honestly. You're a beautiful woman and I haven't had this much fun playing video games in a while."

"Th-Thanks. Do you really mean it?"

"If I didn't mean it, I wouldn't have said it, Gloria. I'm an honest man, if I just want to get in your pants, I'd tell you directly. Speaking of which, let's play another cup. I want to turn the tables..."

"Let me just..." I touched his shaft and then his balls. They were oddly squishy, it was kind of funny. "Could you turn around? I want to see your behind." Hm, he looked good. "Thanks. I can see why some people like you."

The next cup was a catastrophe for me. In the first race, I barely lost to James, while in the second it felt like every computer player joined in a team to make me last... Sitting in my underwear, I began the third race and stayed in first place, until the finish line, where a blue shell hit me. I'm surprised it didn't happen sooner, to be honest. Now I sat there topless. Did I want to win? Honestly, yes, even if it's just for the honor. But James was motivated. I was better at driving, getting tight corners, but that never mattered to his brilliant sniping. When you get hit by three green shells, you know you're fighting a formidable opponent.

"Well, Gloria, I'm curious now... I want to see what you have hidden."

"Uhm don't be too mean, I didn't shave recently." With that, I pulled down my underwear. Gloria +1SP (+9SP) I hope he didn't mind the hair.

"No need to worry Gloria, this isn't a jungle, let alone a bush. Just some grass. Besides, it's not the only attraction, is it? Turn around, please."

I did. "Do you like my butt?" Gloria +1SP (+10SP)

"You look great. If your old boyfriends skipped out on you for your body, then I don't know what's wrong with them."

I wanted to get him in the mood, and I had just the right idea... I turned back around and showed him my vagina again, spreading it for him to see. Gloria +4SP (+14SP)

"Now that seems inviting. Mind if I touch there with something else?"

"Actually, I have a better idea. Earn it. We do 8 random tracks. Same rules apply. If we win 4:4, we do what we want. If anyone wins 5:3 or more... that's one sexual favor."

"Anything you'd like to avoid? Total no-go zones?"

"None if you agree the same?"

"Deal."

The race was on. And it was a feisty one. In our seven rounds we had barely played a third of the tracks, so most of these were ones we hadn't played before. I won the first race and James won the second. Then we played a track we played before and James beat me easily. He was a quick learner. The next two tracks went to me. He'd have to beat me in all races if he wanted to get anything out of me. Sadly, that was quite easy, as the sixth track was a repeat track again and he handed my ass to me. The seventh track was a challenging one, but due to poor luck, I lost again. It all came down to the final track. It was a fierce struggle and we traded first and second places a lot. Eventually, he sniped me with a banana peel and caused me to fall off and land in fifth. Goddamn, he got good super fast.

"Congrats on winning 5:3, what do you have in mind?"

"Let me just make it fair." He pulled down his underwear. He spent a long time looking at me and thinking, and his penis got erect by it. It was charming, in all honesty.

"Thinking that long?"

"Well, part of me wants to see if you'd actually follow through, but the race is over and I don't need to be so competitive or mean anymore. What I pulled off at the end was mean enough already." He was lost in thought again for a bit. "Let's go for a middle of the road situation. What do you think about anal?"

I simply bent over the couch and pushed my ass up. I made a promise, after all. It won't end this way the next time. "I'm honestly curious if I can take it. But it's your favor, so..." Gloria +9SP (+23SP)

"Gloria, forget the game and the promise for a moment. If you ever feel uncomfortable, tell me, okay? Last time I did anal I was too rough because that's how Donna likes it, she had to spend her weekend in a spa. Little bit of office gossip for you..." He chuckled to himself. I never thought Donna would be this delicate.

"Nah, I loosened it a bit ages ago. It's always simpler to offer a guy anal when you actually want him instead of hoping he has condoms. Just don't be too rough and I should avoid Donna's fate." That and... being able to handle anal is sometimes a benefit when a guy decides on a relationship. I feel like some wouldn't have made it to a second date if it wasn't for that.

"Alright." With that word, his tip had entered. "You were lubricated well enough down there, Gloria... Do you like anal?"

He began to push in more. "A bit, honestly. Never got why some women dislike it. But it's nothing problematic for me." I could feel my pelvic area tighten around his penis as it entered ever deeper. This thing was huge, and he just kept on pushing and pushing. Eventually, he stopped, and I felt impaled. He then slowly began to move around his dick, back and forth, gradually increasing pace. In a weird way, he kept me on the edge the entire time. Just as I had gotten used to his speed, he went faster. But it didn't feel awful. I enjoyed it a lot. His dick reached far into me.

"I'm going to cum. Inside or outside?"

"Don't care, it's anal." He came inside. It felt oddly good to have his cum stick up there.